Teddy Sheringham has insisted Harry Kane must consider his options this summer amid speculation he could leave Tottenham Hotspur.
The England captain is tied down to the club until 2024 and is the club's top-earner.
However, Kane refused to rule out leaving Spurs if he felt the club weren't moving forward.
"It's one of those things, I couldn't say yes, I couldn't say no. I love Spurs, I'll always love Spurs. But it's one of those things - I've always said if I don't feel we're progressing as a team or going in the right direction, then I'm not someone to just stay there for the sake of it," he said in March.
"I'm an ambitious player, I want to improve, I want to get better, I want to become one of the top, top players.
"It all depends on what happens as a team and how we progress as a team. So it's not a definite I'm going to stay there forever - but it's not a no either."
Following on from those comments, speculation has surrounded Kane about a potential exit, in his search for trophies.
Sheringham endured a similar spell in his career where he just missed out on silverware before winning the treble with Manchester United.
He believes that Kane is happy at Spurs but agrees his career is at a crossroads and he must consider his future if the club don't progress forward next season.
"There are similarities but you have to look at where they are and where Tottenham were when I was playing for them," Sheringham told The Football Show.
"I think the ambition had been sucked out of the club when I was at Tottenham, we weren't really going places. At least with Tottenham at the moment they're getting in the top four, they're challenging for things, they were in the Champions League final not long ago.
"He's got to work out his situation, does he want to leave? Will there be top players coming to Tottenham to play with him, or does he have to leave to play with top players?
"At the moment, I'd say his career at Tottenham has been steadily going forward but I think it might be at a crossroad. If not this year, if they haven't won anything or look like they're challenging for things and moving forwards, there could be changes.
"Harry only has one career and he wants to win things. We'll see what happens but my advice would be 'you only get one career, Harry, make sure you make the most of it."
